Synthesis and biological evaluation of N-substituted-3,5-diphenyl-2-pyrazoline derivatives as cyclooxygenase (COX-2) inhibitors

Otto, 1995, Prostaglandin endoperoxide synthases-1 and -2, J. Lipid Mediat. Cell Signal., 12, 139, 10.1016/0929-7855(95)00015-I Carter, 1998, Recently reported inhibitors of cyclooxygenase-2, Expert Opin. Ther. Pat., 8, 21, 10.1517/13543776.8.1.21 Laneuville, 1994, Differential inhibition of human prostaglandin endoperoxide H synthases-1 and -2 by nonsteroidal anti-inflammatory drugs, J. Pharmacol. Exp. Ther., 271, 927 O’Neill, 1994, Overexpression of human prostaglandin G/H synthase-1 and -2 by recombinant vaccinia virus: inhibition by nonsteroidal anti-inflammatory drugs and biosynthesis of 15-hydroxyeicosatetraenoic acid, Mol. Pharm., 45, 245 Marnett, 1999, Cyclooxygenase 2 inhibitors: discovery, selectivity and the future, Trends Pharmacol. Sci., 20, 465, 10.1016/S0165-6147(99)01385-1 Dannhardt, 2001, Cyclooxygenase inhibitors - current status and future prospects, Eur. J. Med. Chem., 36, 109, 10.1016/S0223-5234(01)01197-7 Almansa, 2003, Synthesis and structure-activity relationship of a new series of COX-2 selective inhibitors: 1,5-Diarylimidazoles, J. Med. Chem., 46, 3463, 10.1021/jm030765s Mitchell, 1993, Selectivity of nonsteroidal antiinflammatory drugs as inhibitors of constitutive and inducible cyclooxygenase, Proc. Natl. Acad. Sci. U.S.A., 90, 11693, 10.1073/pnas.90.24.11693 Tewari, 2001, Synthesis and anti-inflammatory activities of N4, N5-disubstituted 3-methyl-1H-pyrazolo[3,4-c]pyridazines, Bioorg. Med. Chem., 9, 715, 10.1016/S0968-0896(00)00285-6 1993, 1 Amir, 2005, Synthesis and anti-inflammatory, analgesic, ulcerogenic and lipid peroxidation activities of 3,5-dimethyl pyrazoles, 3-methyl pyrazol-5-ones and 3,5-disubstituted pyrazolines, Indian J. Chem. Sect. B. Org. Chem. Incl. Med. Chem., 44B, 2532 Gursoy, 2000, Synthesis and preliminary evaluation of new 5-pyrazolinone derivatives as analgesic agents, Eur. J. Med. Chem., 35, 359, 10.1016/S0223-5234(00)00117-3 Kumar, 2003, Synthesis and anti-inflammatory, analgesic, ulcerogenic and cyclooxygenase activities of novel quinazolinyl-∆2-pyrazolines, Indian J. Chem. Sect. B. Org. Chem. Incl. Med. Chem., 42B, 1979 Chimenti, 2005, Synthesis, molecular modeling studies, and selective inhibitory activity against monoamine oxidase of 1-thiocarbamoyl-3,5-diaryl-4,5-dihydro-(1H)- pyrazole derivatives, J.Med.Chem., 48, 7113, 10.1021/jm040903t Chimenti, 2006, Synthesis, biological evaluation and 3D-QSAR of 1,3,5-trisubstituted-4,5-dihydro-(1H)-pyrazole derivatives as potent and highly selective monoamine oxidase A inhibitors, Curr. Med. Chem., 13, 1411, 10.2174/092986706776872907 Chimenti, 2008, Synthesis, molecular modeling studies and selective inhibitory activity against MAO of N1-propanoyl-3,5-diphenyl-4,5-dihydro-(1H)-pyrazole derivatives, Eur. J. Med. Chem., 43, 2262, 10.1016/j.ejmech.2007.12.026 Chimenti, 2009, Synthesis, molecular modeling, and selective inhibitory activity against human monoamine oxidases of 3-carboxamido-7-substituted coumarins, J. Med. Chem., 52, 1935, 10.1021/jm801496u Berman, 2000, The protein data bank, Nucleic Acids Res., 28, 235, 10.1093/nar/28.1.235 Gupta, 2004, The 2.0 A resolution crystal structure of prostaglandin H2 synthase-1: structural insights into an unusual peroxidase, J. Mol. Biol., 335, 503, 10.1016/j.jmb.2003.10.073 Kurumbail, 1996, Structural basis for selective inhibition of cyclooxygenase-2 by anti-inflammatory agents, Nature, 384, 644, 10.1038/384644a0 Trott, 2010, AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading, J. Comput. Chem., 31, 455 Procopio, 2009, Synthesis, biological evaluation, and molecular modeling of oleuropein and its semisynthetic derivatives as cyclooxygenase inhibitors, J. Agric. Food Chem., 57, 11161, 10.1021/jf9033305 Alcaro, 2000, A “quasi-flexible” automatic docking processing for studying stereoselective recognition mechanisms. part I. protocol validation, J. Comput. Chem., 21, 515, 10.1002/(SICI)1096-987X(200005)21:7<515::AID-JCC2>3.0.CO;2-5 Alcaro, 2007, “Quasi flexible” automatic docking processing for studying stereoselective recognition mechanisms, part 2: prediction of ∆∆ G of complexation and 1H-NMR NOE correlation, J. Comput. Chem., 28, 1119, 10.1002/jcc.20655